US5512664A - Monoazo dye for thermal transfer printing - Google Patents

Monoazo dye for thermal transfer printing Download PDF

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Publication number
US5512664A
US5512664A US08/359,579 US35957994A US5512664A US 5512664 A US5512664 A US 5512664A US 35957994 A US35957994 A US 35957994A US 5512664 A US5512664 A US 5512664A
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United States
Prior art keywords
sub
dye
monoazo dye
thermal transfer
following formula
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Expired - Fee Related
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US08/359,579
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English (en)
Inventor
Ki-taek Lee
Young-soup Son
Woo-seok Han
Soon-yeol Eom
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Hansol Paper Co Ltd
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Hansol Paper Co Ltd
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Assigned to HANSOL PAPER CO., LTD. reassignment HANSOL PAPER CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: EOM, SOON-YEOL, HAN, WOO-SEOK, LEE, KI-TAEK, SON, YOUNG-SOUP
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/38235—Contact thermal transfer or sublimation processes characterised by transferable colour-forming materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/388—Azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0846—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by heterocyclic ring linked directly to the benzene ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments

Definitions

  • the present invention relates to a monoazo dye for thermal transfer printing, and especially to an imido-substituted monoazo dye for a sublimable magenta dye used in thermal transfer printing, which has good hue, gray and dye stability.
  • thermal transfer printing systems have been widely used in facsimile and copying machines, and have been further developed such that prints can be obtained from pictures generated electronically from a color video camera or computer.
  • a thermal transfer printing system using a sublimable dye has been developed.
  • an electronically generated picture is first subjected to color separation by color filters.
  • the respective color-separated images are then converted into electrical signals which are operated on to produce Y (yellow), M (magenta) and C (cyan) electrical signals.
  • Y yellow
  • M magenta
  • C cyan
  • Sublimable yellow, magenta and cyan dyes which are heat-transferable, are applied to a sheet-like substrate in the form of an ink, to form a transfer sheet. This is then placed in contact with the material to be printed, that is, a receiving sheet.
  • the two sheets are then inserted between a thermal printing head and a platen roller.
  • the thermal printing head hammer heating elements and is heated sequentially in response to the yellow, magenta and cyan signals.
  • the transfer sheet is selectively heated in accordance with a pattern information signal corresponding to one color, so that dye from the selectively heated regions of the transfer sheet is sublimated and transferred to the receiving sheet and thereby forms a pattern thereon, the form and density of which is in accordance with the pattern and intensity of the heat applied to the transfer sheet.
  • the process is then repeated for the other two colors, and by combining the three colors, a full-color hard copy is obtained which corresponds to the original picture viewed on a screen.
  • a sublimable dye for thermal transfer printing must satisfy several conditions. That is, such a dye should exhibit: (a) sufficient mobility so as to sublime while not thermally disintegrating during thermal printing head operation; (b) a high molar absorptivity coefficient; (c) stability with respect to light, humidity, heat and various chemicals; (d) good hue and gray characteristics; and (e) facility in manufacture.
  • U.S. Pat. No. 4,698,651 discloses a magenta dye-donor element comprising a substituted 5-arylazoisothiazole
  • U.S. Pat. No. 4,701,439 discloses a yellow dye-donor element having a cyanovinyltetrahydro-quinoline structure
  • U.S. Pat. No. 4,695,287 discloses a cyan dye-donor element comprising a 2-carbamoyl-4- N-(p-substituted aminoaryl)imino!-1,4-naphthoquinone.
  • Patent Laid-open Publication sho 59-78894 discloses a cyan dye having a naphthalene dione structure
  • Japanese Patent Laid-open publication sho 59-227948 discloses a cyan dye having an anthraquinone structure. Many of these dyes, however, do not meet the requirements (a through e) for thermal transfer printing.
  • Japanese Patent Laid-open Publication sho 61-227092 discloses an azo dye having the following structure: ##STR2## wherein Y is hydrogen, alkoxy, methyl or halogen, and X is methyl, methoxy, formylamyl, alkylcarbonylamyl, alkylsulfonylamyl or alkoxycarbonylamyl.
  • Japanese Patent Laid-open Publication sho 62-99195 discloses an azo dye having the following structure: ##STR3## wherein Y is hydrogen, methyl or acylamyl, and X is cyano or halogen.
  • Y is hydrogen, methyl or acylamyl
  • X is cyano or halogen.
  • the object of the present invention is, therefore, to provide a new sublimable magenta monoazo dye for a thermal transfer printing, which exhibits substantial improvement in terms of stability, hue, gray and color development.
  • a magenta monoazo dye for thermal transfer printing having the following Formula (I) ##STR4## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-8 -alkyl, cycloalkyl, aryl, 2-cyanoalkyl, 2-hydroxyalkyl, 2-alkoxyalkyl and 2-acetoxyalkyl;
  • A, B and C are each independently selected from the group consisting of hydrogen, halogen, cyano, nitro, carboxyamino, trifluoromethyl, acetoxy, benzoxy, C 1-4 -alkoxy, C 1-6 -alkyl, alkyl- or aryl-sulfonamino, alkyl- or aryl-sulfonyl, alkyl- or aryl-carbonyl, C 1-6 -hydroxy-alkyl and C 1-6 -alkoxyalkyl;
  • X is hydrogen, C 1-4 -alkyl, C 1-4 -alkoxy or halogen
  • Y is selected from the following substituents, ##STR5## wherein R 3 and R 4 are each independently selected from the group consisting of hydrogen substituted or unsubstituted C 1-4 -alkyl halogen, alkylcarboxylate, and carbonyl ##STR6## represents a cyclized structure where R 3 and R 4 are combined to form saturated or unsaturated cycloalkyl of C 3-6 , or represents a non-cyclized structure where R 3 and R 4 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-4 -alkyl, halogen, alkylcarboxylate, and carbonyl; and
  • Z is nitro, halogen, C 1-4 -alkyl, C 1-4 -alkoxy, sulfonyl, carbonyl, carboxyamide, sulfonamino, cyano, hydroxy or hydrogen.
  • the compounds used in the present invention may be prepared by an established synthetic procedure such as that described in Example 1 below.
  • R 1 and R 2 in the structural Formula (I) are each independently selected from the group consisting of substituted or unsubstituted C 2-3 -alkyl, 2-cyanoethyl and 2-ethoxyethyl.
  • X is hydrogen, methoxy or methyl group.
  • a and B are each independently selected from the group consisting of cyano, bromo, chloro and nitro, and C is chloro, cyano, nitro, fluoro, trifluoromethyl, C 1-2 -alkoxy or bromo.
  • Y is a substituted or unsubstituted succinimide, maleimide, or phthalimide.
  • R 3 and R 4 are each independently C 1-2 -alkyl group, or are combined together to form C 4-5 -saturated or unsaturated cycloalkyl.
  • B is hydrogen or cyano
  • a and C are each independently selected from the group consisting of cyano, nitro, chloro and fluoro.
  • Z is acetamido, nitro, halogen or hydrogen.
  • R 1 and R 2 are each independently C 2-4 -alkyl, X is a hydrogen, Y is succinimide, and A and B are cyano, or C is nitro, preferably show good color development.
  • the compound of the Formula (I) is selected from following compounds: ##STR47##
  • the dye of the present invention may be dispersed and dissolved in an organic solvent with a binder to make an ink composition for thermal transfer.
  • the ink composition may be coated on a substrate to make a transfer sheet.
  • the transfer sheet coated with a dye may be in contact with a receiving sheet, so that the dye is adjacent to the receiving sheet. Then, selective heating and pressing of the back side of the transfer sheet with a thermal printing head results in a selective transferring of the dye to print a desired picture on the receiving sheet.
  • the ink composition containing a dye compound of the present invention preferably comprises: 2-8% by weight of a dye of Formula (I); 2-8% by weight of a binder; and 84-96% by weight of an organic solvent.
  • the amount of the dye is preferably in the range of 2% to 8% by weight. If the amount of the dye is less than 2% by weight, the concentration of the dye transferred is low and the sensitivity of the color development decreases, while an amount of more than 8% by weight leads to problems of solubility and waste.
  • the amount of the binder is preferably in the range of 2-8% by weight of the ink composition. If the amount of the binder is less than 2% by weight, the viscosity of the composition is low and the adhesiveness decreases, so that the dye may easily come off upon coating or after coating. On the other hand, for amounts of binder more than 8% by weight, the viscosity of the composition is so high that the coating process is difficult, the coating layer is uneven, and it is difficult to transfer the dye.
  • the binder may be any resinous or polymeric material suitable for binding the dye to the substrate.
  • suitable binders are cellulose derivatives such as ethylcellulose, hydroxyethylcellulose, methylcellulose, cellulose acetate butyrate; vinyl resins and derivatives thereof such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate, polyacrylamide; polyacrylic acid, polymethylmethacrylate, polycarbonate, polysulfone and polyphenylene oxide.
  • the organic solvent used in the ink composition may be methanol, ethanol, toluene, methylethylketone, cyclohexanone, or N,N-dimethylformamide.
  • the ink composition may also contain other additives, such as curing agents or preservatives.
  • the ink composition may be coated on the substrate to form a dye layer with a preferred thickness of 0.4-2.0 ⁇ m.
  • the substrate for the transfer sheet may be any convenient sheet material capable of withstanding temperature of about 400° C. for periods of approximately 20 milliseconds, yet thin enough to transmit heat applied on one side through to the dye on the other side, to effect transfer to a receiving sheet within 10 milliseconds.
  • suitable materials are polyester such as polyethylene terephthalate, polyamide, polyacrylate, polycarbonate, cellulose ester, fluorine polymer, polyacetal and polyamide.
  • the thickness of the substrate is preferably in the range of 2-15 ⁇ m. If the thickness is less than 2 ⁇ m, the substrate film may be distorted upon contact with a thermal printing head of a high temperature, while thicknesses of more than 15 ⁇ m result in poor heat transfer and decreased thermal transfer sensitivity.
  • the backside of the substrate for a transfer sheet may be coated with a slipping layer to prevent the substrate film from being distorted and to prevent the thermal printing head from sticking to the film.
  • the materials for such a slipping layer may be carboxylate, sulfonate, phosphate, aliphatic amine, polyoxyethylene alkylester, polyethyleneglycol fatty acid ester, silicone oil or synthetic oils.
  • a dye barrier layer may be employed between a substrate film and a dye layer to prevent the dye from thermally transferring to the substrate.
  • the materials for the dye barrier layer may be a hydrophilic polymer such as polyacrylamide, butylmethacrylate, polyvinylalcohol and polyvinylacetate.
  • the receiving sheet usually comprises a substrate having thereon a dye receiving layer.
  • the substrate for the receiving sheet may be polyethylene terephthalate, polyester sulfone, polyamide, cellulose ester, polyester with a white pigment incorporated therein, or a synthetic paper.
  • the dye receiving layer is coated on the substrate to absorb and diffuse the transferred dye more easily.
  • the dye receiving layer may be, for example, polycarbonate, polyurethane, polyester, polyamide, polyvinylchloride, styrene-acrylonitrile copolymer, or polycaprolactam.
  • the dye receiving layer may contain a slipping material, such as wax or silicone oil, to facilitate the separation of the layer after dye transferring.
  • N,N-diethyl-3-succinimido aniline (1 mmol) was dissolved in a mixture of 5 g of water and 0.3 g of concentrated HCl, and then the solution was cooled to 0° C.
  • a solution of 5-anthranilonitrile (1 mmol) in a mixture of 1 ml of concentrated H 2 SO 4 and 0.5ml of glacial acetic acid was dropped gradually in to a solution of sodium nitrite (1 mmol) in 0.5 ml of concentrated H 2 SO 4 below 5° C. Then, the mixed solution was stirred for 30 minutes.
  • a transfer sheet was prepared by applying the ink composition to a sheet of 7 ⁇ m thick polyethylene terephthalate film using a bar coater to give 1 g/m 2 of dry coat, and then drying the coating.
  • Transfer sheets were prepared by the method of Example 1 using compounds as indicated in TABLE 1, in place of Compound 1.
  • a transfer sheet was prepared by the method of Example 1 using Compound A having the following formula, in place of Compound 1. ##STR48##
  • a transfer sheet was prepared by the method of Example 1 using Compound B having the following formula, in place of Compound 1. ##STR49##
  • a color development was assessed using a transfer sheet prepared in each of the above examples and comparative examples and a receiving sheet (Sony, UPC 3010), at the thermal head (TH-FMR) conditions of 22 V and 1.5 W/dot.
  • a color density was determined by densitometer (TR 1224).
  • a receiving sheet which has a dye transfer image formed from the transfer sheet prepared in each of the above examples and comparative Examples was placed at the condition of 35 ⁇ 2° C. and 60 ⁇ 2% RH for 48 hours using a xenon weather-o-meter (Atlas, ES-25). The density loss during the period was determined by the densitometer.
  • the dyes of Formula (I) of the present invention when used as inks for the thermal transfer, all have good or acceptable hue and gray, and show superior dye stability compared to the control dyes of a similar structure.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Coloring (AREA)
US08/359,579 1993-12-30 1994-12-20 Monoazo dye for thermal transfer printing Expired - Fee Related US5512664A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR93-31257 1993-12-30
KR1019930031257A KR970007419B1 (ko) 1993-12-30 1993-12-30 승화형 열전사 기록용 색소

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US (1) US5512664A (enrdf_load_stackoverflow)
JP (1) JPH07223383A (enrdf_load_stackoverflow)
KR (1) KR970007419B1 (enrdf_load_stackoverflow)
CN (1) CN1072247C (enrdf_load_stackoverflow)
CH (1) CH688625A5 (enrdf_load_stackoverflow)
DE (1) DE4446396A1 (enrdf_load_stackoverflow)
FR (1) FR2714673B1 (enrdf_load_stackoverflow)
GB (1) GB2285449B (enrdf_load_stackoverflow)
TW (1) TW283724B (enrdf_load_stackoverflow)

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US20040247916A1 (en) * 2001-09-11 2004-12-09 Macdonald William Alasdair Heat-stabilised poly(ethylene naphthalate) film for flexible electronic and opto-electronics devices
US20100068355A1 (en) * 2006-11-01 2010-03-18 Dupont Teijin Films U.S. Limited Partnership Heat-sealable composite polyester film
US20100159198A1 (en) * 2002-04-12 2010-06-24 Dupont Teijin Films U.S. Limited Partnership Coated polymeric substrates having improved surface smoothness suitable for use in flexible electronic and opto-electronic devices
US20100221391A1 (en) * 2007-08-30 2010-09-02 Fenghua Deng Dual ovenable food package having a thermoformable polyester film lid
CN101332694B (zh) * 2001-09-11 2013-01-23 美国杜邦泰津胶片合伙人有限公司 用于柔性电子器件和光电子器件的热稳定聚萘二甲酸乙二醇酯膜

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US9663515B2 (en) 2014-11-05 2017-05-30 Vitae Pharmaceuticals, Inc. Dihydropyrrolopyridine inhibitors of ROR-gamma
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TW202220968A (zh) 2016-01-29 2022-06-01 美商維它藥物有限責任公司 ＲＯＲ－γ調節劑
US9481674B1 (en) 2016-06-10 2016-11-01 Vitae Pharmaceuticals, Inc. Dihydropyrrolopyridine inhibitors of ROR-gamma
WO2019018975A1 (en) 2017-07-24 2019-01-31 Vitae Pharmaceuticals, Inc. INHIBITORS OF ROR GAMMA
EP3658555A1 (en) 2017-07-24 2020-06-03 Vitae Pharmaceuticals, LLC Inhibitors of ror

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Cited By (13)

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Publication number Priority date Publication date Assignee Title
CN102785419A (zh) * 2001-09-11 2012-11-21 美国杜邦泰津胶片合伙人有限公司 用于柔性电子器件和光电子器件的热稳定聚萘二甲酸乙二醇酯膜
US7101627B2 (en) * 2001-09-11 2006-09-05 Dupont Teijin Films U.S. Limited Partnership Heat-stabilised poly(ethylene naphthalate) film for flexible electronic and opto-electronics devices
US20060275591A1 (en) * 2001-09-11 2006-12-07 Macdonald William A Heat-stabilised poly(ethylene naphthalate) film for flexible electronic and opto-electronic devices
US7300703B2 (en) * 2001-09-11 2007-11-27 Dupont Teijin Films U.S. Limited Partnership Heat-stabilised poly(ethylene naphthalate) film for flexible electronic and opto-electronic devices
CN102785419B (zh) * 2001-09-11 2015-01-14 美国杜邦泰津胶片合伙人有限公司 用于柔性电子器件和光电子器件的热稳定聚萘二甲酸乙二醇酯膜
CN101332694B (zh) * 2001-09-11 2013-01-23 美国杜邦泰津胶片合伙人有限公司 用于柔性电子器件和光电子器件的热稳定聚萘二甲酸乙二醇酯膜
US20040247916A1 (en) * 2001-09-11 2004-12-09 Macdonald William Alasdair Heat-stabilised poly(ethylene naphthalate) film for flexible electronic and opto-electronics devices
US20100154886A1 (en) * 2002-04-12 2010-06-24 Dupont Teijin Films U.S. Limited Partnership Coated polymeric substrates having improved surface smoothness suitable for use in flexible electronic and opto-electronic devices
US8318289B2 (en) * 2002-04-12 2012-11-27 Dupont Teijin Films U.S. Limited Partnership Coated polymeric substrates having improved surface smoothness suitable for use in flexible electronic and opto-electronic devices
US20100159198A1 (en) * 2002-04-12 2010-06-24 Dupont Teijin Films U.S. Limited Partnership Coated polymeric substrates having improved surface smoothness suitable for use in flexible electronic and opto-electronic devices
US8501300B2 (en) 2002-04-12 2013-08-06 Dupont Teijin Films U.S. Limited Partnership Coated polymeric substrates having improved surface smoothness suitable for use in flexible electronic and opto-electronic devices
US20100068355A1 (en) * 2006-11-01 2010-03-18 Dupont Teijin Films U.S. Limited Partnership Heat-sealable composite polyester film
US20100221391A1 (en) * 2007-08-30 2010-09-02 Fenghua Deng Dual ovenable food package having a thermoformable polyester film lid

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TW283724B (enrdf_load_stackoverflow) 1996-08-21
KR950017231A (ko) 1995-07-20
DE4446396A1 (de) 1995-07-06
GB9426163D0 (en) 1995-02-22
KR970007419B1 (ko) 1997-05-08
GB2285449B (en) 1998-03-18
JPH07223383A (ja) 1995-08-22
GB2285449A (en) 1995-07-12
CH688625A5 (fr) 1997-12-15
FR2714673A1 (fr) 1995-07-07
CN1072247C (zh) 2001-10-03
FR2714673B1 (fr) 1998-10-16

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